70877-75-7
Chemical Structure
O-Desmethyl quinidine
Synonym(s): Cupreidine
- CAS No.: 70877-75-7
- Formula:C19H22N2O2
- Molecular Weight:310.40
IUPAC Name: 4-((S)-hydroxy((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)quinolin-6-ol
InChIKey: VJFMSYZSFUWQPZ-WXPXUSHHSA-N
SMILES: O[C@@H](C1=CC=NC2=C1C=C(O)C=C2)[C@]3([H])[N@](C[C@@H]4C=C)CC[C@H]4C3
Biological Activity: O-Desmethyl quinidine (Cupreidine) is a Cinchona alkaloid metabolite and an active product formed by O-demethylation of Quinidine (HY-B1751). It serves as a bifunctional organocatalyst and chiral resolving agent, and catalyzes enantioselective transformations through hydrogen bonding and conformational control. O-Desmethyl quinidine is used in the study of arrhythmias[1][2][3][4][5][6].
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O-Desmethyl quinidine | 99.05% | O-Desmethyl quinidine (Cupreidine) is a Cinchona alkaloid metabolite and an active product formed by O-demethylation of Quinidine (HY-B1751). It serves as a bifunctional organocatalyst and chiral resolving agent, and catalyzes enantioselective transformations through hydrogen bonding and conformational control. O-Desmethyl quinidine is used in the study of arrhythmias. | ||||||||||||||||||||
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References
- [1]. Tamai, G., Yoshida, H., Imai, H. et al. Isolation of new quinidine metabolites and simultaneous determination of quinidine and its metabolites in blood and urine by direct injection HPLC analysis. Chromatographia 20, 671–676 (1985).
- [2]. Maeda K, Takano J, Ikeda Y, Fujita T, Oyama Y, Nozawa K, Kumagai Y, Sugiyama Y. Nonlinear pharmacokinetics of oral quinidine and verapamil in healthy subjects: a clinical microdosing study. Clin Pharmacol Ther. 2011 Aug;90(2):263-70.
- [3]. Marcelli, T., van Maarseveen, J.H. and Hiemstra, H. (2006), Cupreine und Cupreidine: eine außergewöhnliche Klasse von bifunktionalen Cinchona-Organokatalysatoren. Angewandte Chemie, 118: 7658-7666.
- [4]. Qian J, et al. Excited state proton transfer in the Cinchona alkaloid cupreidine. Physical chemistry chemical physics : PCCP. 2010 Oct 21;12(39):12562-9.
- [5]. Nielsen F, et al. Lack of relationship between quinidine pharmacokinetics and the sparteine oxidation polymorphism. European journal of clinical pharmacology. 1995;48(6):501-4.
- [6]. Rakhit A, et al. Improved liquid-chromatographic assay of quinidine and its metabolites in biological fluids. Clinical chemistry. 1982 Jul;28(7):1505-9.
